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#3 - Mike Leake - 5 years, $80 million, 2016
At the time, I don't know a whole lot of fans that liked the Mike Leake contract. Needless to say, those fans were right.
Like all of these deals, it felt like another miss from playing in the "middle of free agency" rather than going after the big fish. Clearly, Leake was not there top target, as the Cardinals were outbid by the Cubs and the Red Sox for Jason Heyward and David Price.
In Leake's one and half seasons in St. Louis, he went 16-24 with a 4.46 ERA in 330.2 innings of work. The Cardinals cut bait with Leake at the 2017 trade deadline, dealing him to Seattle for prospect Rayder Ascanio.
Leake would have been a fine number-five starter for the club, but not at that large of a contract. There was not a ton of upside with Leake to begin with, so it is not surprising this deal turned out so poorly.